Wig knorr



UNITED STATES PATENT OFFICE.

VQRMALS MEISTER, LUCIUS dz GERMANY.

BRUNING, OF II()CIIST-ON-TIIE-MAIN,

MORPHOLIN AND PROCESS OF MAKING sAM'E,

SPEOIFIOATTQN forming part of Letters Patent No. 615,488, dated December 6, 1898..

' Application filed December 29, 1897- Serial No. 884,432. (No specimens.)

action of acid condensation agents intomor- 'phol'm or morpholin derivatives by heating the former with dioxyethylamin derivatives to 100 to 200 centigrade. Condensation agents-may be employed-for instance, concentrated hydrochloric acid, phosphoric acid,

phosphorous pentoxid, and acetic-acid anhydride-the' best results being obtained with moderately concentrated sulfuric acid of about. sixty to seventy per cent. z 5 The effect of the condensation agents is at splitting off of water. of dioxyethylamin into'morpholin is illustrated, for instance, bytho following equation:

By employing hydrochloric acid as a condensation agent a chlorhydrin of dioxyethylamin is produced as an intermediate product,

40 already mentioned by me in the Berliner Beriohte, 1889, p. 2084. The process, however, is, essentially the same in using other condensation agents.

I illustrate my process by the following ex- 4 5 ample: A solution of dioxyethylamin is heated for several hours to about 160 centigrade infive to ten times the quantity of sulfuric acid of seventy per cent; is over-saturated with alkali and distilled with The transformation The product of reaction steam. The morpholin distils over rapidly and completely with the steam. By the evaporation ofthedistillate neutralized with h ydrochloric acid the morpholin hydrochlorate is obtained as a white crystalline mass. From this salt the morpholin may be set free with alkalies. It boils at 128 centigrade. It possessesa characteristic odor similar to that of piperidin,which it resembles completely in its chemical behavior. vielding a nitrosamir. of theboiling-point of 224.5 centi grade, urethan of 220 to 221 centigrade,-benzoyl derivative of the melting-point 74 to 75 centigrade.

or orthooxyethylmethylamidophen01,

OH CH OH ethylam'idophenol,

Morpholin is easily soluble in water, alco- (C -H, I the correspond- NCH CII ing morpholin derivativesviz., one methylmorpholin, boiling-point 115 to 117 centigrade; one ethylmorpholin, boiling-poi at 138 boiling-point 270 centigradeyone oxyethylmorpholin, boiling-point 240 centigrade; phenmorpholin,boiling-point 268 centigrade, and methylphenmorpholin, boiling-point 261 centigrade.

' The morpholins are used as medicaments or as primary products for the manufacture .of the same, acting in doses of 0.1 to one gram as a narcotic.

Having thus described my invention, I claim as new and desire to secure by Letters Patent 1. A process for "the manufacture of morpholins, which consists in heating to from to 200 centigrade the dioxy compounds C-.-C-OH with the. atom complex N 3 C-'C'Oll acid condensation agents, then making the with to 139 centigrade; one phenylmorpholin,

l solution alknline and distilling-with stemn, odor similar: to piperidin, substantially. set

substantially as set forth. forth. v I

2. As anew product, the morpholin'of the In testimony that I,claim the foregoing as formula i my invention I have signed my-name in pres 'C-II ,-CII ence of two subscribing witnesses. NH 7 0,

LUDWIG KNORR. the same-beings liquid boiling at 128 eenti- \Vit'nesses:

"um TEIOHMANN,

grade, easily soluble in water, alcohol, other I 10 and benzene, soluble in acids, and havinga'n ELISABETH KNORR. 

